CH368158A - Verfahren zur Herstellung von 6,7-Dehydro-B-apo-3-carotinal - Google Patents

Verfahren zur Herstellung von 6,7-Dehydro-B-apo-3-carotinal

Info

Publication number: CH368158A
Authority: CH; Switzerland
Prior art keywords: trimethyl; ether; acid; cyclohexen; solution
Prior art date: 1958-02-14

Application number

CH5586958A

Other languages

German (de)

English (en)

Inventor

Herbert Dr Lindlar

Marc Dr Montavon

Gabriel Dr Saucy

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1958-02-14

Filing date

1958-02-14

Publication date

1963-03-31

1958-02-14 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1958-02-14 Priority to CH5586958A priority Critical patent/CH368158A/de

1959-02-02 Priority to BE575323A priority patent/BE575323A/fr

1959-02-13 Priority to ES0247223A priority patent/ES247223A1/es

1963-03-31 Publication of CH368158A publication Critical patent/CH368158A/de

Links

238000000034 method Methods 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 4
239000007859 condensation product Substances 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 5
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
238000010653 organometallic reaction Methods 0.000 claims description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
239000000047 product Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000003208 petroleum Substances 0.000 description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
-1 acetylene compound Chemical class 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
150000001241 acetals Chemical class 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
238000010306 acid treatment Methods 0.000 description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
ZKJNETINGMOHJG-GGWOSOGESA-N (e)-1-[(e)-prop-1-enoxy]prop-1-ene Chemical compound C\C=C\O\C=C\C ZKJNETINGMOHJG-GGWOSOGESA-N 0.000 description 1
XTYLJMKJLMHFJK-UHFFFAOYSA-N 1,1,3,3-tetraethoxy-2-methylpropane Chemical compound CCOC(OCC)C(C)C(OCC)OCC XTYLJMKJLMHFJK-UHFFFAOYSA-N 0.000 description 1
VXYSFSCCSQAYJV-UHFFFAOYSA-N 2-methylpropanedial Chemical compound O=CC(C)C=O VXYSFSCCSQAYJV-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
239000003674 animal food additive Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000021466 carotenoid Nutrition 0.000 description 1
150000001747 carotenoids Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
235000013345 egg yolk Nutrition 0.000 description 1
210000002969 egg yolk Anatomy 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000576 food coloring agent Substances 0.000 description 1
235000002864 food coloring agent Nutrition 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
244000144977 poultry Species 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/14—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by isomerisation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CH5586958A 1958-02-14 1958-02-14 Verfahren zur Herstellung von 6,7-Dehydro-B-apo-3-carotinal CH368158A (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CH5586958A CH368158A (de)	1958-02-14	1958-02-14	Verfahren zur Herstellung von 6,7-Dehydro-B-apo-3-carotinal
BE575323A BE575323A (fr)	1958-02-14	1959-02-02	Procédé pour la préparation d'un aldéhyde polyénique
ES0247223A ES247223A1 (es)	1958-02-14	1959-02-13	PROCEDIMIENTO PARA LA PREPARACION DE UN ALDEHiDO DE POLIENO

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH5586958A CH368158A (de)	1958-02-14	1958-02-14	Verfahren zur Herstellung von 6,7-Dehydro-B-apo-3-carotinal

Publications (1)

Publication Number	Publication Date
CH368158A true CH368158A (de)	1963-03-31

Family

ID=4520144

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH5586958A CH368158A (de)	1958-02-14	1958-02-14	Verfahren zur Herstellung von 6,7-Dehydro-B-apo-3-carotinal

Country Status (3)

Country	Link
BE (1)	BE575323A (fr)
CH (1)	CH368158A (fr)
ES (1)	ES247223A1 (fr)

1958
- 1958-02-14 CH CH5586958A patent/CH368158A/de unknown
1959
- 1959-02-02 BE BE575323A patent/BE575323A/fr unknown
- 1959-02-13 ES ES0247223A patent/ES247223A1/es not_active Expired

Also Published As

Publication number	Publication date
ES247223A1 (es)	1959-10-16
BE575323A (fr)	1959-08-03

Publication	Publication Date	Title
CH628012A5 (de)	1982-02-15	Verfahren zur herstellung von cyklopentenonderivaten.
CH427795A (de)	1967-01-15	Verfahren zur Herstellung von Pyridinderivaten
DE3122995C2 (fr)	1991-08-14
CH368158A (de)	1963-03-31	Verfahren zur Herstellung von 6,7-Dehydro-B-apo-3-carotinal
AT208834B (de)	1960-04-25	Verfahren zur Herstellung von 6,7-Dehydro-ß-apo-3-carotinal
CH371113A (de)	1963-08-15	Verfahren zur Herstellung von 6,7-Dehydro-B-apo-3-carotinal
DE2132315C3 (de)	1975-02-06	Verfahren zur Herstellung der 1 beta, 11 alpha-Dimethyl-1,2,3,4,10 alpha, 11hexahydro-9 beta-hydroxyfluoren-1 alpha, 9alpha-dicarbonsäure aus Abietinsäure
DE962074C (de)	1957-04-18	Verfahren zur Herstellung des 4-[2', 6', 6'-Trimethylcyclohexyliden]-2-methylbuten-(2)-als-(1) (Iso-C-aldehyd) bzw. 4-[2', 6', 6'-Trimethylcyclohexen-(2')-yliden]-2-methylbuten-(2)-als-(1) (Retrodehydro-C-aldehyd)
DE818937C (de)	1951-10-29	Verfahren zur Synthese von Oestron und seinen Abbauprodukten sowie ihren Derivaten und Isomeren
AT202714B (de)	1959-04-10	Verfahren zur Herstellung von Carotinoiden
DE893947C (de)	1953-10-22	Verfahren zur Herstellung ungesaettigter Aldehyde
DE961165C (de)	1957-04-04	Verfahren zur Herstellung des 6-[2', 6', 6'-Trimethylcyclohexyliden]-4-methylhexadien-(2, 4)-als-(1) (Iso-C-aldehyd), des 6-[2', 6', 6',-Trimethylcyclohexen-(2')-yliden]-4-methyl-hexadien-(2', 4)-als-(1) (Retrodehydro-C-aldehyd) bzw. des 6-[2', 6', 6'-Trimethylcyclohexadien-(1', 3')-yl]-4-methyl-hexadien-(2, 4)-als-(1) (ª‰ -Dehydro-C-aldehd)
DE2203807C3 (de)	1980-11-06	Verfahren zur Herstellung von D,L-Menthol
AT203151B (de)	1959-05-11	Verfahren zur Herstellung von Carotinoiden
AT235259B (de)	1964-08-25	Verfahren zur Herstellung von Polyencarbonylverbindungen
CH373373A (de)	1963-11-30	Verfahren zur Herstellung von ungesättigten Ketonen
CH326163A (de)	1957-12-15	Verfahren zur Herstellung von Polyenaldehyden
AT214909B (de)	1961-05-10	Verfahren zur Herstellung von ungesättigten Ketonen
CH326161A (de)	1957-12-15	Verfahren zur Herstellung von Polyenaldehyden
DE1081454B (de)	1960-05-12	Verfahren zur Herstellung von 6, 7-Dehydro-ª‰-apo-3-carotinal
CH362064A (de)	1962-05-31	Verfahren zur Herstellung eines Polyenaldehydes
CH322617A (de)	1957-06-30	Verfahren zur Herstellung eines Polyenaldehyds
DE1000376B (de)	1957-01-10	Verfahren zur Herstellung des 8-[2', 6', 6'-Trimethylcyclohexyliden]-2, 6-dimethyloctatrien-(2, 4, 6)-als-(1) (Iso-C-aldehyd), des 8-[2', 6', 6'-Trimethylcyclohexen-(2')-yliden]-2, 6-dimethyloctatrien-(2, 4, 6)-als-(1) (Retrodehydro-C-aldehyd) bzw. des8-[2', 6', 6'-Trimethylcyclohexadien-(1', 3')-yl]-2, 6-dimethyloctatrien-(2, 4, 6)-als-(1) (ª‰-Dehydro-C-aldehyd)
DE1118191B (de)	1961-11-30	Verfahren zur Herstellung von ungesaettigten Ketonen
DE1020023B (de)	1957-11-28	Verfahren zur Herstellung von Polyenaldehyden